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  • 1
    Electronic Resource
    Electronic Resource
    Substituierte 1-Azaadamantane (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 4073-4085 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Substituted 1-AzaadamantanesSubstituted 1-azaadamantanes of type 14 are facilely prepared from the six-membered rings 2. Functionalized derivatives 2 of cyclohexane are easily synthesized from α,β-unsaturated ketones and dimethyl malonate or by similar procedures. With hexamethylenetetramine as partner the azatricyclic products 14 are formed in one step from 2. The Mannich-type mechanism of the key reaction is discussed, and the 1H NMR data are analyzed.
    Notes: Substituierte 1-Azaadamantane vom Typ 14 können auf einem einfachen Syntheseweg ausgehend vom Sechsringsystem 2 hergestellt werden. Funktionalisierte Cyclohexane vom Typ 2 sind wiederum ausgehend von α,β-ungesättigten Ketonen und Dimethylmalonat leicht zugänglich. Mit Hexamethylentetramin als Partner werden die Adamantanderivate 14 in einem Reaktionsschritt aus 2 aufgebaut. Der Mannich-artige Mechanismus der Schlüsselreaktion zum Tricyclus -wird diskutiert, und die 1H-NMR-Daten der erhaltenen 1-Azaadamantane werden analysiert.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181019
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  • 2
    Electronic Resource
    Electronic Resource
    1-Azaadamantane aus substituierten Phloroglucinen (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 4849-4856 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 1-Azaadamantanes from Substituted PhloroglucinolsThe heterocycles 3 are synthesised from substituted phloroglucinols 2 and hexamethylenetetramine in one step. Special chemical properties of these 1-azaadamantanes are, for example, the formation of a BH3-complex 4 and the stereoselective reduction to the trialcohol 6. The reaction of 6 with trimethoxymethane yields the heterodiamantane 8.
    Notes: Die 1-Azaadamantanderivate 3 werden aus substituierten Phloroglucinen 2 und Hexamethylentetramin einstufig synthetisiert. Die speziellen chemischen Eigenschaften werden an der Boranatreduktion zum Borankomplex 4 sowie der stereoselektiven Reduktion zum Triol 6 demonstriert. 6 liefert mit Trimethoxymethan den Orthoester 8.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181219
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  • 3
    Electronic Resource
    Electronic Resource
    Synthese und Deoxygenierung substituierter 1-Azaadamantan-4,6-dione (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 459-465 
    Details
    ISSN: 0009-2940
    Keywords: 1-Aza-4,6-adamantanedione derivatives synthesis ; Radical deoxygenation, nBu3SnH ; Ammonium salts ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and Deoxygenation of Substituted 1-Azaadamantane-4,6-diones1-Azaadamantanes 5 and a variety of derivatives are accessible by a triple Mannich reaction of 1,3-cyclohexanediones 1 with hexamethylenetetramine to yield the 1-azaadamantane-4,6-diones 2. Deoxygenation of the sterically hindered and non-enolizable β-dioxo group in 2 succeeds by radical processes. Treatment with NaBH4/MeOH and subsequent chlorination give the dichlorides 4, which are dehalogenated with nBu3SnH. Quaternary ammonium salts 6 are available in high yields.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250225
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  • 4
    Electronic Resource
    Electronic Resource
    Azabicyclononane durch Fragmentierung, II. Regiospezifische (Grob-)Fragmentierung zur Darstellung von 3-AzabicyclononanenHerrn Prof. Dr. Eckehard V. Dehmlow zum 60. Geburtstag gewidmet. (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 1137-1140 
    Details
    ISSN: 0009-2940
    Keywords: 3-Azabicyclo[3.3.1]nonanes ; 1-Azaadamantane derivatives ; Clemmensen reduction ; Dichlorination, geminal ; Radical deoxygenation, dehalogenation, nBu3SnH ; Grob fragmentation, regiospecifity ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Azabicyclononanes by Fragmentation, II[1]. - Synthesis of 3-Azabicyclononanes by Regiospecific (Grob) FragmentationClemmensen reduction of the non-enolizable β1-dioxo group in the 1-azaadamantanedione derivative 1 gives the β1-hydroxy ketone 2, which is converted to the thioesters 3. Treatment of 3a or 3b with nBu3SnH/toluene yields the partially deoxygenated monoketone 4. Chlorination of 2 with SOCl2 generates 6 (geminal dichlorination). Dehalogenation with nBu3SnH produces 5. On the other hand, 2 can be monochlorinated to give 7, selectively. Preparative Grob fragmentation of the aza-tricyclic skeleton in 7 regiospecifically provides the 3-azabicyclo[3.3.1]nonane derivative 8. An even better access to 8 from 2 proceeds via an intermediate tosylate.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260512
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  • 5
    Electronic Resource
    Electronic Resource
    β-Aminoketone als Schlüsselverbindungen zur Synthese von Pyridinen: Ein neuartiger, leistungsfähiger Zugang zu kondensierten Bi- und Terpyridinen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 571-576 
    Details
    ISSN: 0009-2940
    Keywords: Annelated pyridines, preparation from Mannich bases ; 5,6-Dihydro-1,10-phenanthrolines, substituted ; 4,5-Diazafluorenes, substituted ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: β-Amino Ketones as Key Intermediates in the Synthesis of Pyridines: A Novel and Efficient Route to Annelated Bi- and TerpyridinesThe hydrochlorides of β-amino ketones 1a - e (Mannich bases) are easily obtained starting compounds for a novel synthesis of pyridines. Condensation with the heteroaromatic ketones 8, 9, and 10 yields 5,6-dihydro-1,10-phenanthrolines 3a - d, 13 and 4,5-diazafluorenes 4a - d, which have not yet been described in literature. Symmetrical terpyridines 3e, 4e are formed in a one-step reaction of 8, 9 with dimethylmethylenammonium chloride in the presence of an ammonia source.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240324
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